5284-29-7

Basic information

• Product Name: 2-Dodecylphenol
• Synonyms: 2-N-DODECYLPHENOL;2-LAURYLPHENOL;2-dodecylphenol;2-N-DODECYLPHENOL 98+%;o-Dodecylphenol
• CAS NO: 5284-29-7
• Molecular Formula: C₁₈H₃₀O
• Molecular Weight: 262.43
• Mol File: 5284-29-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 39°C
• Appearance: /
• CAS DataBase Reference: 2-Dodecylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Dodecylphenol(5284-29-7)
• EPA Substance Registry System: 2-Dodecylphenol(5284-29-7)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-52/53-34
• Safety Statements: 26-36/37/39-61-45
• Hazardous Substances Data: 5284-29-7(Hazardous Substances Data)

Usage

General Description

2-Dodecylphenol is a chemical compound used as an intermediate in the production of antioxidants, lubricating oil additives, and surfactants. It is a member of the alkylphenol group, which are widely used in industrial applications. 2-Dodecylphenol is a colorless to pale yellow liquid with a characteristic phenolic odor. It is soluble in organic solvents and slightly soluble in water. The compound is considered to have low toxicity, but prolonged exposure can cause irritation to the skin and eyes. It is important to handle and store 2-Dodecylphenol with care and follow proper safety precautions to prevent any potential health hazards.

Synthetic route

2-dodecyl(methoxymethoxy)benzene (130296-78-5) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 16h; Inert atmosphere;	99%
With o-toluenesulfonic acid In methanol for 30h;	95%
With toluene-4-sulfonic acid In methanol for 30h; Heating;	95%

2-fluorophenol (367-12-4) + laurylmagnesium bromide (15890-72-9) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With 4-Fluorophenol; dichloro{1,2-bis[di(4-isopropylphenyl)phosphino]benzene}nickel (II) In diethyl ether at 0 - 20℃; Inert atmosphere; regioselective reaction;	79%

2-monochlorophenol (95-57-8) + laurylmagnesium bromide (15890-72-9) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With Ni(1,2-bis(diphenylphosphanyl)-benzene)Cl2; 4-chloro-phenol In diethyl ether at 0 - 20℃; Inert atmosphere; regioselective reaction;	69%

1-dodecylbromide (143-15-7) + methoxybenzene (100-66-3) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
(i) nBuLi, Et2O, THF, hexane, (ii) /BRN= 506159/, (iii) BBr3, CH2Cl2; Multistep reaction;

1-<2-hydroxy-phenyl>-dodecanone-(1) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With hydrogenchloride; amalgamated zinc

O-methoxymethylphenol (824-91-9) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TMEDA, n-BuLi / 1.) THF, hexane, 0 deg C, 1.5 h, 2.) THF, hexane, a) 0 deg C, 1.5 h, b) RT, 12 h 2: 95 percent / TsOH*H2O / methanol / 30 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) n-BuLi, TMEDA / 1.) THF, 0 deg C, 2.) 25 deg C, 12 h 2: 95 percent / toluenesulfonic acid / methanol / 30 h View Scheme

1-dodecylbromide (143-15-7) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TMEDA, n-BuLi / 1.) THF, hexane, 0 deg C, 1.5 h, 2.) THF, hexane, a) 0 deg C, 1.5 h, b) RT, 12 h 2: 95 percent / TsOH*H2O / methanol / 30 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) n-BuLi, TMEDA / 1.) THF, 0 deg C, 2.) 25 deg C, 12 h 2: 95 percent / toluenesulfonic acid / methanol / 30 h View Scheme

1-dodecyl alcohol (112-53-8) + phenol (108-95-2) → 2-t-dodecyl-phenol (5284-29-7)

formaldehyd (50-00-0) + 2-t-dodecyl-phenol (5284-29-7) → C37H60O2

Conditions	Yield
In xylene at 175℃; for 10h;	85%

2-t-dodecyl-phenol (5284-29-7) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-2-dodecylphenyl dimethylcarbamothioate (29665-65-4)

Conditions	Yield
Stage #1: 2-t-dodecyl-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide at 80℃; for 7h;	82%

2-t-dodecyl-phenol (5284-29-7) + lead(IV) tetraacetate (546-67-8) → 6-dodecyl-6-acetoxy-2,4-cyclohexadienone (130296-68-3)

Conditions	Yield
In acetic acid at 25℃; for 10h;	76%

2-t-dodecyl-phenol (5284-29-7) + acetic acid (64-19-7) → 6-dodecyl-6-acetoxy-2,4-cyclohexadienone (130296-68-3)

Conditions	Yield
With lead(IV) acetate at 25℃; for 10h;	72%

formaldehyd (50-00-0) + 2-t-dodecyl-phenol (5284-29-7) → 3-dodecyl-2-hydroxybenzaldehyde

Conditions	Yield
With triethylamine; magnesium chloride In tetrahydrofuran for 16h; Inert atmosphere; Reflux;	69%

2-t-dodecyl-phenol (5284-29-7) + chloroacetic acid ethyl ester (105-39-5) → (2-dodecyl-phenoxy)-acetic acid (20803-58-1)

Conditions	Yield
With sodium ethanolate Erwaermen des Reaktionsprodukts mit wss. NaOH;

2-t-dodecyl-phenol (5284-29-7) + 3-monochloro-1,2-propanediol (96-24-2) → 3-(2-dodecyl-phenoxy)-propane-1,2-diol (97017-05-5)

Conditions	Yield
With sodium ethanolate

carbon dioxide (124-38-9) + 2-t-dodecyl-phenol (5284-29-7) → 3-Dodecyl-2-hydroxy-benzoesaeure, '3-Dodecyl-salicylsaeure' (30908-39-5)

Conditions	Yield
With potassium carbonate at 180℃;

2-t-dodecyl-phenol (5284-29-7) → methyl 6-oxo-4(E)-octadecenoate (130296-70-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation 3: 80 percent / Na2CO3 / methanol / 1 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl 6-acetoxyoctadeca-3(Z),5(E)-dienoate (130296-69-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation View Scheme
Multi-step reaction with 2 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl (3R*,6R*)-6-dodecyl-3,6-dihydro-6-methoxy-1,2-dioxine-3-acetate (130296-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: 1.) O2, rose bengal (RB), 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 1 h, 2.) 25 deg C, 40 h View Scheme
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) O2, CuSO4, 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 12 h, 2.) 25 deg C, 30 h View Scheme
Multi-step reaction with 3 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation 3: 1.) O2, 2.) p-toluenesulfonic acid / 1.) rose bengal / 1.) CH2Cl2, MeOH, irradiation, 10 deg C, 8 h, 2.) 25 deg C, 40 h View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl (3R*,6S*)-6-dodecyl-3,6-dihydro-6-methoxy-1,2-dioxine-3-acetate (130296-76-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: 1.) O2, rose bengal (RB), 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 1 h, 2.) 25 deg C, 40 h View Scheme
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) O2, CuSO4, 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 12 h, 2.) 25 deg C, 30 h View Scheme
Multi-step reaction with 3 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation 3: 1.) O2, 2.) p-toluenesulfonic acid / 1.) rose bengal / 1.) CH2Cl2, MeOH, irradiation, 10 deg C, 8 h, 2.) 25 deg C, 40 h View Scheme

2-t-dodecyl-phenol (5284-29-7) → 6-oxo-4(E)-octadecenoic acid (138286-35-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: aq. NaOH / tetrahydrofuran / 1 h / 50 °C View Scheme

2-t-dodecyl-phenol (5284-29-7) → 6-oxo-4-hydroxyoctadecanoic acid (138286-36-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: aq. NaOH / tetrahydrofuran / 1 h / 50 °C View Scheme

2-t-dodecyl-phenol (5284-29-7) → 4-Methoxy-6-oxo-octadecanoic acid methyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → 6-oxo-4-octadecanoic lactone (138286-38-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: aq. NaOH / tetrahydrofuran / 1 h / 50 °C 6: 90 percent / rose bengal lactone (RBL) / CH2Cl2; methanol / 6 h View Scheme
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h 6: 32 percent / rose bengal lactone (RBL) / CH2Cl2; methanol / 12 h / Irradiation View Scheme

2-t-dodecyl-phenol (5284-29-7) → tert-butyldimethylsilyl 6-oxo-4(E)-octadecenoate (138286-37-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl 6-methoxy-3(Z),5-octadecadienoate (130296-79-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: TsOH*H2O / benzene / 3.5 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl 6-methoxy-3(E),5-octadecadienoate (130296-71-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: TsOH*H2O / benzene / 3.5 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → (3R*,6R*)-6-dodecyl-3,6-dihydro-1,2-dioxine-3-acetic acid (138286-40-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h 6: rose bengal lactone (RBL) / CH2Cl2; methanol / 12 h / Irradiation View Scheme

2-t-dodecyl-phenol (5284-29-7) → (3R*,6S*)-6-dodecyl-3,6-dihydro-1,2-dioxine-3-acetic acid (138286-39-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h 6: rose bengal lactone (RBL) / CH2Cl2; methanol / 12 h / Irradiation View Scheme

Upstream product

• 143-15-7 1-dodecylbromide 
• 100-66-3 methoxybenzene 
• 95-57-8 2-monochlorophenol 
• 15890-72-9 laurylmagnesium bromide 
• 367-12-4 2-fluorophenol 
• 112-53-8 1-dodecyl alcohol 
• 108-95-2 phenol 
• 824-91-9 O-methoxymethylphenol 
• 130296-78-5 2-dodecyl(methoxymethoxy)benzene 

Downstream Products

• 29665-65-4 O-2-dodecylphenyl dimethylcarbamothioate 
• 29688-04-8 S-2-dodecylphenyl dimethylcarbamothioate 
• 1296884-94-0 o-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1296885-05-6 o-dodecylbenzenesulfonyl chloride 
• 30908-39-5 3-Dodecyl-2-hydroxy-benzoesaeure, '3-Dodecyl-salicylsaeure' 
• 130296-68-3 6-dodecyl-6-acetoxy-2,4-cyclohexadienone 
• 78576-60-0 C₃₇H₆₀O₂ 
• 97017-05-5 3-(2-dodecyl-phenoxy)-propane-1,2-diol 
• 20803-58-1 (2-dodecyl-phenoxy)-acetic acid 

Relevant articles and documents

Salen-Based Amphiphiles: Directing Self-Assembly in Water by Metal Complexation

Tuning morphologies of self-assembled structures in water is a major challenge. Herein we present a salen-based amphiphile which, using complexation with distinct transition metal ions, allows to control effectively the self-assembly morphology in water, as observed by Cryo-TEM and confirmed by DLS measurements. Applying this strategy with various metal ions gives a broad spectrum of self-assembled structures starting from the same amphiphilic ligand (from cubic structures to vesicles and micelles). Thermogravimetric analysis and electric conductivity measurements reveal a key role for water coordination apparently being responsible for the distinct assembly behavior.

Total synthesis of (±)-chondrillin, (±)-plakorin, and related peroxy ketals. development of a general route to 3,6-dihydro-1,2-dioxin-3-ols

Seven-step syntheses of the antitumor cyclic peroxy ketals la, 2a, chondrillin (Ib), and plakorin (2b) from (methoxymethoxy)benzene (8) have been achieved in 26-28% overall yields. The key step is the photooxygenation of enone 4 with a sun lamp using rose bengal lactone or CuSO4 as a sensitizer which gives a mixture of peroxy hemiketals 15 and 16 in 75-85% yields. Acetal formation in acidic methanol completes the syntheses of 1 and 2. The mechanism of photooxygenation was ascertained using 3-nonen-2-one (22) as a model for 4. Irradiation converts 22 to the cis-enone 23 which undergoes photoenolization to give 24. Dienol 24 undergoes a sensitized reaction with oxygen to give 29 and 30. The detailed mechanism of this last step is not known, although singlet oxygen is probably not involved. This reaction is general for any enone or enal which can undergo photoenolization to give a dienol. Peroxy hemiketals 33a, 41, and 43-46 were prepared in 30-80% yields. Peroxy ketals can be used for the synthesis of furans, diones, and pyridazines.

Synthesis of antitumor cyclic peroxy ketals related to chrondrillin and xestins A and B

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